Organic light emitting device

ABSTRACT

Provided is an organic light-emitting device comprising: a light emitting layer comprising a compound of the following Chemical Formula 1, and one or more of an electron transport layer, an electron injection layer, or an electron transport and injection layer that comprises at least one of a compound of the following Chemical Formula 2 and a compound of the following Chemical Formula 3: 
     
       
         
         
             
             
         
       
     
     wherein Ar 2  and Ar 3  are each independently a substituent of Chemical Formula 4, 
     
       
         
         
             
             
         
       
     
     where X 1  to X 5  are each independently N or C(R 8 ), wherein at least two of X 1  to X 5  are N, and the other substituents are as defined in the specification. The organic light emitting device including the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 or 3 had significantly superior efficiency and lifespan.

CROSS-REFERENCE TO RELATED APPLICATION(S)

This application is a National Stage Application of International Application No. PCT/KR2022/002859 filed on Feb. 28, 2022, which claims priority to and the benefit of Korean Patent Application No. 10-2021-0030418 filed on Mar. 8, 2021 in the Korean Intellectual Property Office, the disclosures of which are incorporated herein by reference in their entirety.

TECHNICAL FIELD

The present disclosure relates to an organic light emitting device.

BACKGROUND

In general, an organic light emitting phenomenon refers to a phenomenon where electric energy is converted into light energy by using an organic material. The organic light emitting device using the organic light emitting phenomenon has characteristics such as a wide viewing angle, an excellent contrast, a fast response time, an excellent luminance, driving voltage and response speed, and thus many studies have proceeded.

The organic light emitting device generally has a structure which comprises an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer frequently has a multilayered structure that comprises different materials in order to enhance efficiency and stability of the organic light emitting device, and for example, the organic material layer can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, the holes are injected from an anode into the organic material layer and the electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, an exciton is formed, and light is emitted when the exciton falls to a ground state again.

There is a continuing need for the development of new materials for the organic materials used in the organic light emitting devices as described above.

PRIOR ART LITERATURE Patent Literature

-   (Patent Literature 0001) Korean Unexamined Patent Publication No.     10-2000-0051826 -   (Patent Literature 0002) US Patent Publication No. 2007-0196692 -   (Patent Literature 0003) Korean Unexamined Patent Publication No.     10-2017-0048159 -   (Patent Literature 0004) U.S. Pat. No. 6,821,643

DETAILED DESCRIPTION OF THE INVENTION Technical Problem

The present disclosure relates to an organic light emitting device.

Technical Solution

In the present disclosure, provided is an organic light emitting device including:

-   -   an anode;     -   a hole transport layer;     -   a light emitting layer;     -   an electron transport layer, an electron injection layer, or an         electron transport and injection layer; and     -   a cathode,     -   wherein the light emitting layer includes a compound of the         following Chemical Formula 1, and     -   the electron transport layer, the electron injection layer, or         the electron transport and injection layer includes at least one         of the compound of the following Chemical Formula 2 and the         compound of Chemical Formula 3 below:

-   -   wherein in the Chemical Formula 1:     -   Z is O or S;     -   L₁ is a direct bond or a substituted or unsubstituted C₆₋₆₀         arylene;     -   Ar₁ is a substituted or unsubstituted C₆₋₆₀ aryl;     -   R₁ to R₃ are each independently hydrogen, deuterium, or a         substituted or unsubstituted C₆₋₆₀ aryl, or two adjacent         substituents thereof combine to form a benzene ring;     -   n is an integer of 0 to 8;     -   m is an integer of 0 to 4; and     -   is an integer of 0 to 3;

-   -   wherein in the Chemical Formula 2 or 3:     -   R₄ to R₇ are each independently hydrogen or deuterium;     -   p1 to p4 are an integer of 1 to 4;     -   L₂ and L₃ are each independently a direct bond or a substituted         or unsubstituted C₆₋₆₀ arylene; and     -   Ar₂ and Ar₃ are each independently a substituent of Chemical         Formula 4:

-   -   wherein in the Chemical Formula 4:     -   X₁ to X₅ are each independently N or C(R⁸), wherein at least two         of X₁ to X₅ are N; and

each R₈ is independently hydrogen, deuterium, a substituted or unsubstituted C₁₋₂₀ alkyl, a substituted or unsubstituted C₆₋₆₀ aryl, or a substituted or unsubstituted C₂₋₆₀ heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or two adjacent R₈s combine to form a benzene ring.

Advantageous Effects

The above-described organic light emitting device controls the compound included in the light emitting layer and the electron transport layer, thereby improving efficiency, low driving voltage, and/or lifespan of the organic light emitting device.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron transport and injection layer 5, and a cathode 6.

FIG. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron transport and injection layer 5, and a cathode 6.

DETAILED DESCRIPTION OF THE EMBODIMENTS

Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the invention.

As used herein, the notation

, or

means a bond linked to another substituent group.

As used herein, the term “substituted or unsubstituted” means being unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthioxy group, an arylthioxy group, an alkylsulfoxy group, an arylsulfoxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group containing at least one of N, O and S atoms, or being unsubstituted or substituted with a substituent in which two or more substituents of the above-exemplified substituents are connected. For example, “a substituent in which two or more substituents are connected” can be a biphenyl group. Namely, a biphenyl group can be an aryl group, or it can also be interpreted as a substituent in which two phenyl groups are connected.

In the present disclosure, the carbon number of a carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group can be a compound having the following structural formulae, but is not limited thereto:

In the present disclosure, an ester group can have a structure in which oxygen of the ester group is substituted by a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group can be a compound having the following structural formulae, but is not limited thereto:

In the present disclosure, the carbon number of an imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group can be a compound having the following structural formulae, but is not limited thereto:

In the present disclosure, a silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like, but is not limited thereto.

In the present disclosure, a boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

In the present disclosure, examples of a halogen group include fluorine, chlorine, bromine, or iodine.

In the present disclosure, the alkyl group can be straight-chain, or branched-chain, and the carbon number thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present disclosure, the alkenyl group can be straight-chain or branched-chain, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

In the present disclosure, a cycloalkyl group is not particularly limited, but the carbon number thereof is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present disclosure, an aryl group is not particularly limited, but the carbon number thereof is preferably 6 to 60, and it can be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The monocyclic aryl group includes a phenyl group, a biphenyl group, a terphenyl group and the like, but is not limited thereto. The polycyclic aryl group includes a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group or the like, but is not limited thereto.

In the present disclosure, a fluorenyl group can be substituted, and two substituents can be bonded to each other to form a spiro structure. In the case where the fluorenyl group is substituted,

and the like can be formed. However, the structure is not limited thereto.

In the present disclosure, a heterocyclic group is a heterocyclic group containing at least one heteroatom of O, N, Si and S as a heterogeneous element, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazol group, an oxadiazol group, a triazol group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazol group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but are not limited thereto.

In the present disclosure, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the aforementioned examples of the aryl group. In the present disclosure, the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group is the same as the aforementioned examples of the alkyl group. In the present disclosure, the heteroaryl in the heteroarylamine can apply the aforementioned description of the heterocyclic group. In the present disclosure, the alkenyl group in the aralkenyl group is the same as the aforementioned examples of the alkenyl group. In the present disclosure, the aforementioned description of the aryl group can be applied except that the arylene is a divalent group. In the present disclosure, the aforementioned description of the heterocyclic group can be applied except that the heteroarylene is a divalent group. In the present disclosure, the aforementioned description of the aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group but formed by combining two substituent groups. In the present disclosure, the aforementioned description of the heterocyclic group can be applied, except that the heterocycle is not a monovalent group but formed by combining two substituent groups.

In the present disclosure, provided is an organic light emitting device including an anode; a hole transport layer; a light emitting layer; an electron transport layer, an electron injection layer, or an electron transport and injection layer; and a cathode, wherein the light emitting layer includes a compound of Chemical Formula 1, and the electron transport layer, the electron injection layer, or the electron transport and injection layer includes at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3.

The organic light emitting device according to the present disclosure controls the compound included in the light emitting layer and the compound included in the electron transport layer, the electron injection layer, or the electron transport and injection layer, thereby improving efficiency, low driving voltage, and/or lifespan of the organic light emitting device.

Hereinafter, the present invention will be described in detail for each configuration.

Anode and Cathode

As the anode material, generally, a material having a large work function is preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chrome, copper, zinc, and gold, or an alloy thereof; metal oxides such as zinc oxides, indium oxides, indium tin oxides (ITO), and indium zinc oxides (IZO); a combination of metals and oxides, such as ZnO:Al or SnO₂:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, and the like, but are not limited thereto.

As the cathode material, generally, a material having a small work function is preferably used so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multilayered structure material such as LiF/Al or LiO₂/Al, and the like, but are not limited thereto.

Hole Injection Layer

The organic light emitting device according to the present disclosure can include a hole injection layer between the anode and the hole transport layer, if necessary.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound which has a capability of transporting the holes, thus has a hole injecting effect in the anode and an excellent hole-injecting effect to the light emitting layer or the light emitting material, prevents excitons produced in the light emitting layer from moving to an electron injection layer or the electron injection material, and is excellent in the ability to form a thin film.

It is preferable that a HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and a HOMO of a peripheral organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, an arylamine-based organic material, a hexanitrilehexaazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, polyaniline and polythiophene-based conductive polymer, and the like, but are not limited thereto.

Hole Transport Layer

In addition, the hole transport layer is a layer that receives holes from an anode or a hole injection layer formed on the anode and transports the holes to the light emitting layer. The hole transport material is suitably a material having large mobility to the holes, which can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugate portion and a non-conjugate portion are present together, and the like, but are not limited thereto.

Electron Blocking Layer

The organic light emitting device according to the present disclosure can include an electron blocking layer between a hole transport layer and a light emitting layer, if necessary. The electron blocking layer is a layer which is formed on the hole transport layer, is preferably provided in contact with the light emitting layer, and thus serves to control hole mobility, to prevent excessive movement of electrons, and to increase the probability of hole-electron bonding, thereby improving the efficiency of the organic light emitting device. The electron blocking layer includes an electron blocking material, and an arylamine-based organic material can be used as the electron blocking material, but is not limited thereto.

Light Emitting Layer

The light emitting material included in the light emitting layer is suitably a material capable of emitting light in a visible ray region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, to combine them, and having good quantum efficiency to fluorescence or phosphorescence. The light emitting layer can include a host material and a dopant material, and the compound of Chemical Formula 1 can be included as a host in the present disclosure.

Preferably, L₁ is a direct bond, phenylene, biphenylene, or naphthylene; and the phenylene, biphenylene, or naphthylene is each independently unsubstituted or substituted with deuterium.

Preferably, Ar₁ is phenyl, biphenylyl, naphthyl, or phenanthrenyl; and the phenyl, biphenylyl, naphthyl, or phenanthrenyl is each independently unsubstituted or substituted with deuterium.

Preferably, R₁ to R₃ are each independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents thereof are combined to form a benzene ring; and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.

Preferably, each R₁ is independently hydrogen or deuterium; each R₂ or R₃ is independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents thereof are combined to form a benzene ring; and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.

Preferably, the compound of Chemical Formula 1 contains at least one deuterium.

Representative examples of the compound of Chemical Formula 1 are as follows:

In addition, the present disclosure provides a method for preparing a compound of Chemical Formula 1, as shown in Reaction Scheme 1 below.

In the Reaction Scheme 1, Z, L₁, Ar₁, R₁ to R₃, n, m, and o are as defined above, and NBS is N-bromosuccinimide.

The above reaction uses a Suzuki coupling reaction, and can be more specifically described in Examples described below.

Hole Blocking Layer

The organic light emitting device according to the present disclosure includes a hole blocking layer between the light emitting layer and the electron transport layer, if necessary. Preferably, the hole blocking layer is in contact with the light emitting layer.

The hole blocking layer serves to improve the efficiency of an organic light emitting device by suppressing holes injected from the anode from being transferred to the cathode without recombination in the light emitting layer. Specific examples of the hole blocking material include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like, but are not limited thereto.

Electron Transport Layer, Electron Injection Layer, or Electron Transport and Injection Layer

The organic light emitting device according to the present disclosure can include an electron transport layer, an electron injection layer, or an electron transport and injection layer between the light emitting layer and the cathode.

The electron transport layer is a layer which receives electrons from a cathode or an electron injection layer formed on the cathode and transports the electrons to a light emitting layer, and can suppress the transfer of holes in the light emitting layer. An electron transport material is suitably a material which can receive electrons well from a cathode and transport the electrons to a light emitting layer, and at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 can be included in the present disclosure.

The electron injection layer is a layer which injects electrons from an electrode, and the electron injection material is preferably a compound which can transport electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons produced from the light emitting layer from moving to a hole injection layer, and is also excellent in the ability to form a thin film. In the present disclosure, at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 can be included

The electron transport and injection layer is a layer capable of simultaneously performing electron transport and electron injection, and can include at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3.

Preferably, the Chemical Formula 2 is the following Chemical Formula 2-1; and the Chemical Formula 3 is the following Chemical Formula 3-1:

in the Chemical Formula 2-1 or 3-1, L₂, L₃, Ar₂ and Ar₃ are as defined above.

Preferably, L₂ and L₃ are each independently a direct bond, phenylene, or biphenyldiyl.

Preferably, Ar₂ and Ar₃ are each independently any one selected from the group consisting of:

wherein in the above group, R₈ is as defined above.

Preferably, each R₈ is independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, or two adjacent R₈s are combined to form a benzene ring; and the phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl is each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.

Preferably, Ar₂ and Ar₃ are each independently any one selected from the group consisting of:

Representative examples of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 are as follows:

In addition, the present disclosure provides a method for preparing a compound of Chemical Formula 2 or a compound of Chemical Formula 3, as shown in Reaction Schemes 2 to 5 below.

In the Reaction Schemes 2 to 5, each L is independently L₂ or L₃; each Ar is independently Ar₂ or Ar₃; each R is independently any one of R₄ to R₇; and each p is independently any one of p1 to p4. In addition, L₂, L₃, Ar₂, Ar₃, R₄ to R₇, and p1 to p4 are as defined above, and X is halogen, preferably bromo, or chloro.

In addition, the electron transport layer can further include a metal complex compound. Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)-beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but are not limited thereto.

In addition, the electron injection layer can further include a metal complex compound. Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)-beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but are not limited thereto.

Organic Light Emitting Device

A structure of the organic light emitting device according to the present disclosure is illustrated in FIG. 1 . FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron transport and injection layer 5, and a cathode 6.

In addition, FIG. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 8, a light emitting layer 4, a hole blocking layer 9, an electron transport and injection layer 5, and a cathode 6.

The organic light emitting device according to the present disclosure can be manufactured by sequentially laminating the above-described components. In this case, the organic light emitting device can be manufactured by depositing a metal, metal oxides having conductivity, or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method to form an anode, forming the above-mentioned respective layers thereon, and then depositing a material that can be used as the cathode thereon. In addition to such a method, the organic light emitting device can be manufactured by sequentially depositing the above-described components from a cathode material to an anode material in the reverse order on a substrate (WO 2003/012890). Further, the light emitting layer can be formed using the host and the dopant by a solution coating method as well as a vacuum deposition method. Herein, the solution coating method means a spin coating, a dip coating, a doctor blading, an inkjet printing, a screen printing, a spray method, a roll coating, or the like, but is not limited thereto.

The organic light emitting device according to the present disclosure can be a front side emission type, a backside emission type, or a double-sided emission type according to the used material.

Hereinafter, preferred examples are presented to help the understanding of the present invention. However, these examples are presented for illustrative purposes only, and are not intended to limit the scope of the present disclosure.

PREPARATION EXAMPLES Preparation Example 1-1: Preparation of Compound B1

B1-A (20 g, 60 mmol) and B1-B (12.7 g, 60 mmol) were added to tetrahydrofuran (400 ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (24.9 g, 180.1 mmol) was dissolved in water (25 ml), and then added thereto. Thereafter, it was stirred sufficiently, followed by adding tetrakistriphenyl-phosphinopalladium (2.1 g, 1.8 mmol). After 1 hour of reaction, cooling was performed to room temperature. Then, the organic layer was separated from the water layer, and then the organic layer was distilled. Then, this was dissolved again in chloroform (20 times, 505 mL), and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound B1 in the form of solid (12.6 g, 50%).

MS: [M+H]⁺=421

Preparation Example 1-2: Preparation of Compound B2

Compound B2-A was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used as in the above reaction scheme (MS: [M+H]⁺=471).

Structural Formula B2-A (40.9 g, 86.9 mmol) and AlCl₃ (0.5 g) were added to C₆D₆ (400 ml) and stirred for 2 hours. After completion of the reaction, D₂O (60 ml) was added, and stirred for 30 minutes, followed by adding trimethylamine (6 ml) dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract was dried with anhydrous magnesium sulfate (MgSO₄) and recrystallized with ethyl acetate to obtain Structural Formula B2 (21.4 g, 50%).

MS: [M+H]⁺=493

Preparation Example 1-3: Preparation of Compound B3

Compound B3 was prepared in the same manner as in Preparation Example 1-2, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=521

Preparation Example 1-4: Preparation of Compound B4

Compound B4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=479

Preparation Example 1-5: Preparation of Compound B5

Compound B5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=434

Preparation Example 2-1: Preparation of Compound E1

E1-A (20 g, 64.1 mmol) and E1-B (55.8 g, 128.2 mmol) were added to tetrahydrofuran (400 ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (26.6 g, 192.3 mmol) was dissolved in water (27 ml), and then added thereto. Thereafter, it was stirred sufficiently, followed by adding tetrakistriphenyl-phosphinopalladium (2.2 g, 1.9 mmol). After 1 hour of reaction, cooling was performed to room temperature. Then, the organic layer was separated from the water layer, and then the organic layer was distilled. Then, this was dissolved again in chloroform (20 times, 986 mL), and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound E1 in the form of white solid (32.5 g, 66%).

MS: [M+H]⁺=769

Preparation Example 2-2: Preparation of Compound E2

Compound E2 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=767

Preparation Example 2-3: Preparation of Compound E3

Compound E3 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=715

Preparation Example 2-4: Preparation of Compound E4

Compound E4 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=615

Preparation Example 2-5: Preparation of Compound E5

Compound E5 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=619

Preparation Example 2-6: Preparation of Compound E6

Compound E6 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=715

Preparation Example 2-7: Preparation of Compound E7

Compound E7 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=919

Preparation Example 2-8: Preparation of Compound E8

E8-A (20 g, 47.6 mmol) and E8-B (28 g, 47.6 mmol) were added to 1,4-dioxane (400 ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (30.3 g, 142.9 mmol) was dissolved in water (30 ml), and then added thereto. Thereafter, it was stirred sufficiently, followed by adding dibenzylideneacetonepalladium (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.9 mmol). After 5 hours of reaction, cooling was performed to room temperature, and the resulting solid was filtered. The resulting solid was dissolved again in chloroform (30 times, 1207 mL), and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound E8 in the form of white solid (6 g, 15%).

MS: [M+H]⁺=845

Preparation Example 2-9: Preparation of Compound E9

Compound E9 was prepared in the same manner as in Preparation Example 2-8, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=769

Preparation Example 2-10: Preparation of Compound E10

Compound E10 was prepared in the same manner as in Preparation Example 2-8, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=843

Preparation Example 2-11: Preparation of Compound E11

Compound E11 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=769

Preparation Example 2-12: Preparation of Compound E12

Compound E12 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=715

Preparation Example 2-13: Preparation of Compound E13

Compound E13 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=795

Preparation Example 2-14: Preparation of Compound E14

Compound E14 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=869

Preparation Example 2-15: Preparation of Compound E15

Compound E15 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=919

Preparation Example 2-16: Preparation of Compound E16

Compound E16 was prepared in the same manner as in Preparation Example 2-8, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=768

Preparation Example 2-17: Preparation of Compound E17

Compound E17 was prepared in the same manner as in Preparation Example 2-8, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=845

Preparation Example 2-18: Preparation of Compound E18

Compound E18 was prepared in the same manner as in Preparation Example 2-8, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=775

Preparation Example 2-19: Preparation of Compound E19

Compound E19 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=921

Preparation Example 2-20: Preparation of Compound E20

Compound E20 was prepared in the same manner as in Preparation Example 2-1, except that each starting material was used as in the above reaction scheme.

MS: [M+H]⁺=919

EXPERIMENTAL EXAMPLES Experimental Example 1

A glass substrate on which ITO (Indium Tin Oxide) was coated as a thin film to a thickness of 1,000 Å was put into distilled water in which a detergent was dissolved, and ultrasonically cleaned. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Then, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum depositor.

On the prepared ITO transparent electrode, the following Compound HI-A was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, hexaazatriphenylene (HAT, 50 Å) with the following formula and the following Compound HT-A (600 Å) were sequentially vacuum-deposited to form a hole transport layer.

Then, the following Compounds B1 and BD were vacuum-deposited on the hole transport layer at a weight ratio of 25:1 to a thickness of 200 Å to form a light emitting layer.

The Compound E1 and the following Compound LiQ (Lithium quinolate) were vacuum-deposited on the light emitting layer at a weight ratio of 1:1 to a thickness of 350 Å to form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were sequentially deposited to a thickness of 10 Å and 1,000 Å, respectively to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec. In addition, the degree of vacuum during the deposition was maintained at 1×10⁻⁷ to 5×10⁻⁸ torr, thereby manufacturing an organic light emitting device.

Experimental Examples 2 to 100

An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound B1 or Compound E1.

Comparative Experimental Examples 1 to 251

An organic light emitting device was manufactured in the same manner

as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound B1 or Compound E1. At this time, Compounds BH-1 to BH-4, and ET-1 to ET-19 listed in Table 1 are as follows.

For the organic light emitting devices, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm². In addition, T₉₀, which is the time taken until the initial luminance decreases to 90% at a current density of 20 mA/cm², was measured. The results are shown in Table 1 below.

TABLE 1 Compound (Electron Voltage Efficiency Chromaticity T₉₀ Compound transport and (V@10 (cd/A@10 coordinates (hr@20 (BH) injection layer) mA/cm²) mA/cm²) (x, y) mA/cm²) Experimental B1 E1 3.62 4.70 (0.133, 0.088) 200 Example 1 Experimental B1 E2 3.76 4.65 (0.133, 0.088) 184 Example 2 Experimental B1 E3 3.80 4.56 (0.133, 0.087) 178 Example 3 Experimental B1 E4 3.92 4.20 (0.133, 0.088) 164 Example 4 Experimental B1 E5 3.99 4.15 (0.135, 0.087) 167 Example 5 Experimental B1 E6 3.91 4.14 (0.133, 0.088) 160 Example 6 Experimental B1 E7 3.80 4.61 (0.133, 0.088) 180 Example 7 Experimental B1 E8 3.66 4.75 (0.133, 0.087) 194 Example 8 Experimental B1 E9 3.69 4.61 (0.133, 0.088) 208 Example 9 Experimental B1 E10 3.69 4.75 (0.133, 0.088) 188 Example 10 Experimental B1 E11 3.66 4.65 (0.133, 0.088) 208 Example 11 Experimental B1 E12 3.73 4.76 (0.133, 0.088) 180 Example 12 Experimental B1 E13 3.77 4.66 (0.133, 0.087) 173 Example 13 Experimental B1 E14 3.69 4.56 (0.133, 0.088) 220 Example 14 Experimental B1 E15 3.73 4.57 (0.133, 0.088) 180 Example 15 Experimental B1 E16 3.69 4.61 (0.133, 0.088) 204 Example 16 Experimental B1 E17 3.67 4.65 (0.133, 0.088) 202 Example 17 Experimental B1 E18 3.73 4.42 (0.133, 0.087) 188 Example 18 Experimental B1 E19 3.69 4.61 (0.133, 0.088) 205 Example 19 Experimental B1 E20 3.73 4.56 (0.133, 0.088) 203 Example 20 Experimental B2 E1 3.66 5.17 (0.133, 0.091) 196 Example 21 Experimental B2 E2 3.80 5.12 (0.133, 0.090) 180 Example 22 Experimental B2 E3 3.84 5.02 (0.133, 0.091) 175 Example 23 Experimental B2 E4 3.96 4.61 (0.133, 0.091) 161 Example 24 Experimental B2 E5 4.03 4.57 (0.133, 0.090) 164 Example 25 Experimental B2 E6 3.95 4.55 (0.133, 0.091) 157 Example 26 Experimental B2 E7 3.84 5.07 (0.133, 0.091) 177 Example 27 Experimental B2 E8 3.69 5.22 (0.133, 0.090) 190 Example 28 Experimental B2 E9 3.73 5.07 (0.133, 0.091) 204 Example 29 Experimental B2 E10 3.73 5.22 (0.133, 0.091) 184 Example 30 Experimental B2 E11 3.69 5.12 (0.133, 0.090) 204 Example 31 Experimental B2 E12 3.77 5.23 (0.133, 0.091) 176 Example 32 Experimental B2 E13 3.80 5.13 (0.133, 0.091) 169 Example 33 Experimental B2 E14 3.73 5.02 (0.133, 0.090) 216 Example 34 Experimental B2 E15 3.77 5.02 (0.133, 0.091) 176 Example 35 Experimental B2 E16 3.73 5.07 (0.133, 0.091) 200 Example 36 Experimental B2 E17 3.71 5.12 (0.133, 0.090) 198 Example 37 Experimental B2 E18 3.77 4.86 (0.133, 0.091) 184 Example 38 Experimental B2 E19 3.73 5.07 (0.133, 0.091) 201 Example 39 Experimental B2 E20 3.77 5.02 (0.133, 0.090) 199 Example 40 Experimental B3 E1 3.37 4.94 (0.133, 0.090) 320 Example 41 Experimental B3 E2 3.50 4.89 (0.133, 0.089) 294 Example 42 Experimental B3 E3 3.54 4.79 (0.133, 0.090) 286 Example 43 Experimental B3 E4 3.64 4.40 (0.133, 0.090) 263 Example 44 Experimental B3 E5 3.72 4.36 (0.133, 0.089) 268 Example 45 Experimental B3 E6 3.64 4.34 (0.133, 0.090) 256 Example 46 Experimental B3 E7 3.54 4.84 (0.133, 0.090) 289 Example 47 Experimental B3 E8 3.40 4.98 (0.133, 0.089) 310 Example 48 Experimental B3 E9 3.43 4.84 (0.133, 0.090) 333 Example 49 Experimental B3 E10 3.43 4.98 (0.133, 0.090) 301 Example 50 Experimental B3 E11 3.40 4.89 (0.133, 0.089) 333 Example 51 Experimental B3 E12 3.47 4.99 (0.133, 0.090) 288 Example 52 Experimental B3 E13 3.50 4.89 (0.133, 0.090) 276 Example 53 Experimental B3 E14 3.43 4.79 (0.133, 0.089) 353 Example 54 Experimental B3 E15 3.47 4.80 (0.133, 0.090) 288 Example 55 Experimental B3 E16 3.43 4.84 (0.133, 0.090) 326 Example 56 Experimental B3 E17 3.42 4.89 (0.133, 0.089) 323 Example 57 Experimental B3 E18 3.47 4.64 (0.133, 0.090) 301 Example 58 Experimental B3 E19 3.43 4.84 (0.133, 0.090) 328 Example 59 Experimental B3 E20 3.47 4.79 (0.133, 0.089) 325 Example 60 Experimental B4 E1 3.48 5.03 (0.133, 0.091) 240 Example 61 Experimental B4 E2 3.61 4.98 (0.133, 0.090) 221 Example 62 Experimental B4 E3 3.65 4.88 (0.133, 0.091) 214 Example 63 Experimental B4 E4 3.76 4.49 (0.133, 0.091) 197 Example 64 Experimental B4 E5 3.84 4.44 (0.133, 0.090) 201 Example 65 Experimental B4 E6 3.76 4.43 (0.133, 0.091) 192 Example 66 Experimental B4 E7 3.65 4.93 (0.133, 0.091) 216 Example 67 Experimental B4 E8 3.51 5.08 (0.133, 0.090) 233 Example 68 Experimental B4 E9 3.54 4.93 (0.133, 0.091) 250 Example 69 Experimental B4 E10 3.54 5.08 (0.133, 0.091) 226 Example 70 Experimental B4 E11 3.51 4.98 (0.133, 0.090) 250 Example 71 Experimental B4 E12 3.58 5.09 (0.133, 0.091) 216 Example 72 Experimental B4 E13 3.62 4.99 (0.133, 0.091) 207 Example 73 Experimental B4 E14 3.55 4.88 (0.133, 0.090) 265 Example 74 Experimental B4 E15 3.58 4.89 (0.133, 0.091) 216 Example 75 Experimental B4 E16 3.55 4.93 (0.133, 0.091) 245 Example 76 Experimental B4 E17 3.53 4.98 (0.133, 0.090) 242 Example 77 Experimental B4 E18 3.58 4.73 (0.133, 0.091) 226 Example 78 Experimental B4 E19 3.54 4.93 (0.133, 0.091) 246 Example 79 Experimental B4 E20 3.58 4.88 (0.133, 0.090) 244 Example 80 Experimental B5 E1 3.62 4.70 (0.133, 0.088) 300 Example 81 Experimental B5 E2 3.76 4.65 (0.133, 0.088) 276 Example 82 Experimental B5 E3 3.80 4.56 (0.133, 0.087) 268 Example 83 Experimental B5 E4 3.92 4.20 (0.133, 0.088) 246 Example 84 Experimental B5 E5 3.99 4.15 (0.135, 0.087) 251 Example 85 Experimental B5 E6 3.91 4.14 (0.133, 0.088) 240 Example 86 Experimental B5 E7 3.80 4.61 (0.133, 0.088) 270 Example 87 Experimental B5 E8 3.66 4.75 (0.133, 0.087) 291 Example 88 Experimental B5 E9 3.69 4.61 (0.133, 0.088) 312 Example 89 Experimental B5 E10 3.69 4.75 (0.133, 0.088) 282 Example 90 Experimental B5 E11 3.66 4.65 (0.133, 0.088) 312 Example 91 Experimental B5 E12 3.73 4.76 (0.133, 0.088) 270 Example 92 Experimental B5 E13 3.77 4.66 (0.133, 0.087) 259 Example 93 Experimental B5 E14 3.69 4.56 (0.133, 0.088) 331 Example 94 Experimental B5 E15 3.73 4.57 (0.133, 0.088) 270 Example 95 Experimental B5 E16 3.69 4.61 (0.133, 0.088) 306 Example 96 Experimental B5 E17 3.67 4.65 (0.133, 0.088) 303 Example 97 Experimental B5 E18 3.73 4.42 (0.133, 0.087) 282 Example 98 Experimental B5 E19 3.69 4.61 (0.133, 0.088) 308 Example 99 Experimental B5 E20 3.73 4.56 (0.133, 0.088) 305 Example 100 Comparative B1 ET-1 4.47 1.66 (0.133, 0.088) 44 Experimental Example 1 Comparative B1 ET-2 4.38 1.65 (0.133, 0.087) 42 Experimental Example 2 Comparative B1 ET-3 4.05 1.88 (0.133, 0.088) 52 Experimental Example 3 Comparative B1 ET-4 4.09 1.86 (0.135, 0.087) 51 Experimental Example 4 Comparative B1 ET-5 4.01 2.26 (0.133, 0.088) 122 Experimental Example 5 Comparative B1 ET-6 4.18 1.82 (0.133, 0.088) 78 Experimental Example 6 Comparative B1 ET-7 4.22 1.81 (0.133, 0.087) 76 Experimental Example 7 Comparative B1 ET-8 4.02 2.35 (0.133, 0.088) 140 Experimental Example 8 Comparative B1 ET-9 4.30 1.79 (0.135, 0.087) 75 Experimental Example 9 Comparative B1 ET-10 4.43 1.73 (0.133, 0.088) 147 Experimental Example 10 Comparative B1 ET-11 4.69 1.72 (0.133, 0.088) 110 Experimental Example 11 Comparative B1 ET-12 4.70 1.36 (0.133, 0.087) 32 Experimental Example 12 Comparative B1 ET-13 4.23 3.32 (0.133, 0.088) 129 Experimental Example 13 Comparative B1 ET-14 4.19 3.36 (0.133, 0.088) 116 Experimental Example 14 Comparative B1 ET-15 4.44 3.26 (0.133, 0.088) 131 Experimental Example 15 Comparative B1 ET-16 4.49 3.19 (0.133, 0.087) 132 Experimental Example 16 Comparative B1 ET-17 4.53 3.09 (0.133, 0.088) 136 Experimental Example 17 Comparative B1 ET-18 4.40 3.13 (0.133, 0.088) 135 Experimental Example 18 Comparative B1 ET-19 4.42 1.81 (0.133, 0.088) 100 Experimental Example 19 Comparative B2 ET-1 4.52 1.83 (0.133, 0.091) 43 Experimental Example 20 Comparative B2 ET-2 4.43 1.82 (0.133, 0.090) 41 Experimental Example 21 Comparative B2 ET-3 4.09 2.07 (0.133, 0.091) 51 Experimental Example 22 Comparative B2 ET-4 4.14 2.05 (0.133, 0.091) 50 Experimental Example 23 Comparative B2 ET-5 4.05 2.48 (0.133, 0.090) 120 Experimental Example 24 Comparative B2 ET-6 4.22 2.01 (0.133, 0.091) 76 Experimental Example 25 Comparative B2 ET-7 4.26 1.99 (0.133, 0.091) 75 Experimental Example 26 Comparative B2 ET-8 4.06 2.59 (0.133, 0.090) 137 Experimental Example 27 Comparative B2 ET-9 4.34 1.97 (0.133, 0.091) 73 Experimental Example 28 Comparative B2 ET-10 4.47 1.91 (0.133, 0.091) 144 Experimental Example 29 Comparative B2 ET-11 4.74 1.89 (0.133, 0.090) 108 Experimental Example 30 Comparative B2 ET-12 4.74 1.49 (0.133, 0.091) 31 Experimental Example 31 Comparative B2 ET-13 4.28 3.65 (0.133, 0.091) 126 Experimental Example 32 Comparative B2 ET-14 4.23 3.69 (0.133, 0.090) 114 Experimental Example 33 Comparative B2 ET-15 4.49 3.58 (0.133, 0.091) 129 Experimental Example 34 Comparative B2 ET-16 4.53 3.51 (0.133, 0.091) 130 Experimental Example 35 Comparative B2 ET-17 4.58 3.40 (0.133, 0.090) 134 Experimental Example 36 Comparative B2 ET-18 4.45 3.44 (0.133, 0.091) 132 Experimental Example 37 Comparative B2 ET-19 4.46 1.99 (0.133, 0.091) 98 Experimental Example 38 Comparative B3 ET-1 4.16 1.74 (0.133, 0.090) 70 Experimental Example 39 Comparative B3 ET-2 4.08 1.74 (0.133, 0.089) 67 Experimental Example 40 Comparative B3 ET-3 3.77 1.97 (0.133, 0.090) 83 Experimental Example 41 Comparative B3 ET-4 3.81 1.95 (0.133, 0.090) 82 Experimental Example 42 Comparative B3 ET-5 3.73 2.37 (0.133, 0.089) 195 Experimental Example 43 Comparative B3 ET-6 3.88 1.91 (0.133, 0.090) 125 Experimental Example 44 Comparative B3 ET-7 3.92 1.90 (0.133, 0.090) 122 Experimental Example 45 Comparative B3 ET-8 3.74 2.47 (0.133, 0.089) 224 Experimental Example 46 Comparative B3 ET-9 4.00 1.88 (0.133, 0.090) 120 Experimental Example 47 Comparative B3 ET-10 4.12 1.82 (0.133, 0.090) 235 Experimental Example 48 Comparative B3 ET-11 4.36 1.80 (0.133, 0.089) 176 Experimental Example 49 Comparative B3 ET-12 4.37 1.43 (0.133, 0.090) 51 Experimental Example 50 Comparative B3 ET-13 3.94 3.49 (0.133, 0.090) 206 Experimental Example 51 Comparative B3 ET-14 3.90 3.52 (0.133, 0.089) 186 Experimental Example 52 Comparative B3 ET-15 4.13 3.42 (0.133, 0.090) 210 Experimental Example 53 Comparative B3 ET-16 4.17 3.35 (0.133, 0.090) 212 Experimental Example 54 Comparative B3 ET-17 4.22 3.25 (0.133, 0.089) 218 Experimental Example 55 Comparative B3 ET-18 4.09 3.28 (0.133, 0.090) 216 Experimental Example 56 Comparative B3 ET-19 4.11 1.90 (0.133, 0.090) 160 Experimental Example 57 Comparative B4 ET-1 4.30 1.78 (0.133, 0.091) 52 Experimental Example 58 Comparative B4 ET-2 4.21 1.77 (0.133, 0.090) 50 Experimental Example 59 Comparative B4 ET-3 3.89 2.01 (0.133, 0.091) 62 Experimental Example 60 Comparative B4 ET-4 3.93 1.99 (0.133, 0.091) 61 Experimental Example 61 Comparative B4 ET-5 3.85 2.41 (0.133, 0.090) 146 Experimental Example 62 Comparative B4 ET-6 4.01 1.95 (0.133, 0.091) 94 Experimental Example 63 Comparative B4 ET-7 4.05 1.93 (0.133, 0.091) 92 Experimental Example 64 Comparative B4 ET-8 3.86 2.51 (0.133, 0.090) 168 Experimental Example 65 Comparative B4 ET-9 4.13 1.91 (0.133, 0.091) 90 Experimental Example 66 Comparative B4 ET-10 4.25 1.85 (0.133, 0.091) 176 Experimental Example 67 Comparative B4 ET-11 4.50 1.84 (0.133, 0.090) 132 Experimental Example 68 Comparative B4 ET-12 4.51 1.45 (0.133, 0.091) 38 Experimental Example 69 Comparative B4 ET-13 4.07 3.56 (0.133, 0.091) 155 Experimental Example 70 Comparative B4 ET-14 4.02 3.59 (0.133, 0.090) 139 Experimental Example 71 Comparative B4 ET-15 4.27 3.48 (0.133, 0.091) 157 Experimental Example 72 Comparative B4 ET-16 4.31 3.41 (0.133, 0.091) 159 Experimental Example 73 Comparative B4 ET-17 4.35 3.31 (0.133, 0.090) 164 Experimental Example 74 Comparative B4 ET-18 4.23 3.34 (0.133, 0.091) 162 Experimental Example 75 Comparative B4 ET-19 4.24 1.94 (0.133, 0.091) 120 Experimental Example 76 Comparative B5 ET-1 4.47 1.66 (0.133, 0.088) 65 Experimental Example 77 Comparative B5 ET-2 4.38 1.65 (0.133, 0.088) 62 Experimental Example 78 Comparative B5 ET-3 4.05 1.88 (0.133, 0.087) 78 Experimental Example 79 Comparative B5 ET-4 4.09 1.86 (0.133, 0.088) 76 Experimental Example 80 Comparative B5 ET-5 4.01 2.26 (0.135, 0.087) 183 Experimental Example 81 Comparative B5 ET-6 4.18 1.82 (0.133, 0.088) 117 Experimental Example 82 Comparative B5 ET-7 4.22 1.81 (0.133, 0.088) 115 Experimental Example 83 Comparative B5 ET-8 4.02 2.35 (0.133, 0.087) 210 Experimental Example 84 Comparative B5 ET-9 4.30 1.79 (0.133, 0.088) 112 Experimental Example 85 Comparative B5 ET-10 4.43 1.73 (0.133, 0.088) 220 Experimental Example 86 Comparative B5 ET-11 4.69 1.72 (0.133, 0.088) 165 Experimental Example 87 Comparative B5 ET-12 4.70 1.36 (0.133, 0.088) 48 Experimental Example 88 Comparative B5 ET-13 4.23 3.32 (0.133, 0.087) 193 Experimental Example 89 Comparative B5 ET-14 4.19 3.36 (0.133, 0.088) 174 Experimental Example 90 Comparative B5 ET-15 4.44 3.26 (0.133, 0.088) 197 Experimental Example 91 Comparative B5 ET-16 4.49 3.19 (0.133, 0.088) 199 Experimental Example 92 Comparative B5 ET-17 4.53 3.09 (0.133, 0.088) 205 Experimental Example 93 Comparative B5 ET-18 4.40 3.13 (0.133, 0.087) 203 Experimental Example 94 Comparative B5 ET-19 4.42 1.81 (0.133, 0.088) 150 Experimental Example 95 Comparative BH-1 E1 3.98 4.09 (0.133, 0.091) 40 Experimental Example 96 Comparative BH-1 E2 4.14 4.05 (0.133, 0.090) 37 Experimental Example 97 Comparative BH-1 E3 4.18 3.97 (0.133, 0.091) 36 Experimental Example 98 Comparative BH-1 E4 4.31 3.65 (0.133, 0.091) 33 Experimental Example 99 Comparative BH-1 E5 4.39 3.61 (0.133, 0.090) 33 Experimental Example 100 Comparative BH-1 E6 4.31 3.60 (0.133, 0.091) 32 Experimental Example 101 Comparative BH-1 E7 4.18 4.01 (0.133, 0.091) 36 Experimental Example 102 Comparative BH-1 E8 4.02 4.13 (0.133, 0.090) 39 Experimental Example 103 Comparative BH-1 E9 4.06 4.01 (0.133, 0.091) 42 Experimental Example 104 Comparative BH-1 E10 4.06 4.13 (0.133, 0.091) 38 Experimental Example 105 Comparative BH-1 E11 4.02 4.05 (0.133, 0.090) 42 Experimental Example 106 Comparative BH-1 E12 4.10 4.14 (0.133, 0.091) 36 Experimental Example 107 Comparative BH-1 E13 4.14 4.06 (0.133, 0.091) 35 Experimental Example 108 Comparative BH-1 E14 4.06 3.97 (0.133, 0.090) 44 Experimental Example 109 Comparative BH-1 E15 4.10 3.97 (0.133, 0.091) 36 Experimental Example 110 Comparative BH-1 E16 4.06 4.01 (0.133, 0.091) 41 Experimental Example 111 Comparative BH-1 E17 4.04 4.05 (0.133, 0.090) 40 Experimental Example 112 Comparative BH-1 E18 4.10 3.84 (0.133, 0.091) 38 Experimental Example 113 Comparative BH-1 E19 4.06 4.01 (0.133, 0.091) 41 Experimental Example 114 Comparative BH-1 E20 4.10 3.97 (0.133, 0.091) 41 Experimental Example 115 Comparative BH-2 E1 3.87 4.23 (0.133, 0.092) 60 Experimental Example 116 Comparative BH-2 E2 4.03 4.19 (0.133, 0.091) 55 Experimental Example 117 Comparative BH-2 E3 4.07 4.10 (0.133, 0.092) 54 Experimental Example 118 Comparative BH-2 E4 4.19 3.78 (0.133, 0.092) 49 Experimental Example 119 Comparative BH-2 E5 4.27 3.74 (0.133, 0.091) 50 Experimental Example 120 Comparative BH-2 E6 4.19 3.72 (0.133, 0.092) 48 Experimental Example 121 Comparative BH-2 E7 4.07 4.15 (0.133, 0.092) 54 Experimental Example 122 Comparative BH-2 E8 3.91 4.27 (0.133, 0.091) 58 Experimental Example 123 Comparative BH-2 E9 3.95 4.15 (0.133, 0.092) 62 Experimental Example 124 Comparative BH-2 E10 3.95 4.27 (0.133, 0.092) 56 Experimental Example 125 Comparative BH-2 E11 3.91 4.19 (0.133, 0.091) 62 Experimental Example 126 Comparative BH-2 E12 3.99 4.28 (0.133, 0.092) 54 Experimental Example 127 Comparative BH-2 E13 4.03 4.20 (0.133, 0.092) 52 Experimental Example 128 Comparative BH-2 E14 3.95 4.10 (0.133, 0.091) 66 Experimental Example 129 Comparative BH-2 E15 3.99 4.11 (0.133, 0.092) 54 Experimental Example 130 Comparative BH-2 E16 3.95 4.15 (0.133, 0.092) 61 Experimental Example 131 Comparative BH-2 E17 3.93 4.19 (0.133, 0.091) 61 Experimental Example 132 Comparative BH-2 E18 3.99 3.98 (0.133, 0.092) 56 Experimental Example 133 Comparative BH-2 E19 3.95 4.15 (0.133, 0.092) 62 Experimental Example 134 Comparative BH-2 E20 3.99 4.11 (0.133, 0.091) 61 Experimental Example 135 Comparative BH-3 E1 3.98 4.09 (0.133, 0.091) 50 Experimental Example 136 Comparative BH-3 E2 4.14 4.05 (0.133, 0.090) 46 Experimental Example 137 Comparative BH-3 E3 4.18 3.97 (0.133, 0.091) 45 Experimental Example 138 Comparative BH-3 E4 4.31 3.65 (0.133, 0.091) 41 Experimental Example 139 Comparative BH-3 E5 4.39 3.61 (0.133, 0.090) 42 Experimental Example 140 Comparative BH-3 E6 4.31 3.60 (0.133, 0.091) 40 Experimental Example 141 Comparative BH-3 E7 4.18 4.01 (0.133, 0.091) 45 Experimental Example 142 Comparative BH-3 E8 4.02 4.13 (0.133, 0.090) 49 Experimental Example 143 Comparative BH-3 E9 4.06 4.01 (0.133, 0.091) 52 Experimental Example 144 Comparative BH-3 E10 4.06 4.13 (0.133, 0.091) 47 Experimental Example 145 Comparative BH-3 E11 4.02 4.05 (0.133, 0.090) 52 Experimental Example 146 Comparative BH-3 E12 4.10 4.14 (0.133, 0.091) 45 Experimental Example 147 Comparative BH-3 E13 4.14 4.06 (0.133, 0.091) 43 Experimental Example 148 Comparative BH-3 E14 4.06 3.97 (0.133, 0.090) 55 Experimental Example 149 Comparative BH-3 E15 4.10 3.97 (0.133, 0.091) 45 Experimental Example 150 Comparative BH-3 E16 4.06 4.01 (0.133, 0.091) 51 Experimental Example 151 Comparative BH-3 E17 4.04 4.05 (0.133, 0.090) 51 Experimental Example 152 Comparative BH-3 E18 4.10 3.84 (0.133, 0.091) 47 Experimental Example 153 Comparative BH-3 E19 4.06 4.01 (0.133, 0.091) 51 Experimental Example 154 Comparative BH-3 E20 4.10 3.97 (0.133, 0.091) 51 Experimental Example 155 Comparative BH-4 E1 3.60 4.44 (0.133, 0.092) 90 Experimental Example 156 Comparative BH-4 E2 3.75 4.40 (0.133, 0.091) 83 Experimental Example 157 Comparative BH-4 E3 3.78 4.31 (0.133, 0.092) 80 Experimental Example 158 Comparative BH-4 E4 3.90 3.96 (0.133, 0.092) 74 Experimental Example 159 Comparative BH-4 E5 3.98 3.92 (0.133, 0.091) 75 Experimental Example 160 Comparative BH-4 E6 3.90 3.91 (0.133, 0.092) 72 Experimental Example 161 Comparative BH-4 E7 3.78 4.35 (0.133, 0.092) 81 Experimental Example 162 Comparative BH-4 E8 3.64 4.49 (0.133, 0.091) 87 Experimental Example 163 Comparative BH-4 E9 3.67 4.35 (0.133, 0.092) 94 Experimental Example 164 Comparative BH-4 E10 3.67 4.49 (0.133, 0.092) 85 Experimental Example 165 Comparative BH-4 E11 3.64 4.40 (0.133, 0.091) 94 Experimental Example 166 Comparative BH-4 E12 3.71 4.49 (0.133, 0.092) 81 Experimental Example 167 Comparative BH-4 E13 3.75 4.40 (0.133, 0.092) 78 Experimental Example 168 Comparative BH-4 E14 3.67 4.31 (0.133, 0.091) 99 Experimental Example 169 Comparative BH-4 E15 3.71 4.32 (0.133, 0.092) 81 Experimental Example 170 Comparative BH-4 E16 3.67 4.35 (0.133, 0.092) 92 Experimental Example 171 Comparative BH-4 E17 3.66 4.40 (0.133, 0.091) 91 Experimental Example 172 Comparative BH-4 E18 3.71 4.18 (0.133, 0.092) 85 Experimental Example 173 Comparative BH-4 E19 3.67 4.36 (0.133, 0.092) 92 Experimental Example 174 Comparative BH-4 E20 3.71 4.31 (0.133, 0.091) 91 Experimental Example 175 Comparative BH-1 ET-1 4.92 1.45 (0.133, 0.091) 9 Experimental Example 176 Comparative BH-1 ET-2 4.82 1.44 (0.133, 0.090) 8 Experimental Example 177 Comparative BH-1 ET-3 4.46 1.64 (0.133, 0.091) 10 Experimental Example 178 Comparative BH-1 ET-4 4.50 1.62 (0.133, 0.091) 10 Experimental Example 179 Comparative BH-1 ET-5 4.42 1.96 (0.133, 0.090) 24 Experimental Example 180 Comparative BH-1 ET-6 4.59 1.59 (0.133, 0.091) 16 Experimental Example 181 Comparative BH-1 ET-7 4.64 1.57 (0.133, 0.091) 15 Experimental Example 182 Comparative BH-1 ET-8 4.42 2.04 (0.133, 0.090) 28 Experimental Example 183 Comparative BH-1 ET-9 4.73 1.55 (0.133, 0.091) 15 Experimental Example 184 Comparative BH-1 ET-10 4.87 1.51 (0.133, 0.091) 29 Experimental Example 185 Comparative BH-1 ET-11 5.16 1.49 (0.133, 0.090) 22 Experimental Example 186 Comparative BH-1 ET-12 5.16 1.18 (0.133, 0.091) 6 Experimental Example 187 Comparative BH-1 ET-13 4.66 2.89 (0.133, 0.091) 26 Experimental Example 188 Comparative BH-1 ET-14 4.61 2.92 (0.133, 0.090) 23 Experimental Example 189 Comparative BH-1 ET-15 4.89 2.83 (0.133, 0.091) 26 Experimental Example 190 Comparative BH-1 ET-16 4.94 2.78 (0.133, 0.091) 26 Experimental Example 191 Comparative BH-1 ET-17 4.99 2.69 (0.133, 0.090) 27 Experimental Example 192 Comparative BH-1 ET-18 4.84 2.72 (0.133, 0.091) 27 Experimental Example 193 Comparative BH-1 ET-19 4.86 1.57 (0.133, 0.091) 20 Experimental Example 194 Comparative BH-2 ET-1 4.79 1.50 (0.133, 0.092) 13 Experimental Example 195 Comparative BH-2 ET-2 4.69 1.49 (0.133, 0.092) 12 Experimental Example 196 Comparative BH-2 ET-3 4.34 1.69 (0.133, 0.091) 16 Experimental Example 197 Comparative BH-2 ET-4 4.38 1.68 (0.133, 0.092) 15 Experimental Example 198 Comparative BH-2 ET-5 4.29 2.03 (0.133, 0.092) 37 Experimental Example 199 Comparative BH-2 ET-6 4.47 1.64 (0.133, 0.091) 23 Experimental Example 200 Comparative BH-2 ET-7 4.51 1.62 (0.133, 0.092) 23 Experimental Example 201 Comparative BH-2 ET-8 4.30 2.12 (0.133, 0.092) 42 Experimental Example 202 Comparative BH-2 ET-9 4.60 1.61 (0.133, 0.091) 22 Experimental Example 203 Comparative BH-2 ET-10 4.74 1.56 (0.133, 0.092) 44 Experimental Example 204 Comparative BH-2 ET-11 5.02 1.54 (0.133, 0.092) 33 Experimental Example 205 Comparative BH-2 ET-12 5.02 1.22 (0.133, 0.091) 10 Experimental Example 206 Comparative BH-2 ET-13 4.53 2.99 (0.133, 0.092) 39 Experimental Example 207 Comparative BH-2 ET-14 4.49 3.02 (0.133, 0.092) 35 Experimental Example 208 Comparative BH-2 ET-15 4.75 2.93 (0.133, 0.091) 39 Experimental Example 209 Comparative BH-2 ET-16 4.80 2.87 (0.133, 0.092) 40 Experimental Example 210 Comparative BH-2 ET-17 4.85 2.78 (0.133, 0.092) 41 Experimental Example 211 Comparative BH-2 ET-18 4.71 2.81 (0.133, 0.091) 41 Experimental Example 212 Comparative BH-2 ET-19 4.73 1.63 (0.133, 0.092) 30 Experimental Example 213 Comparative BH-3 ET-1 4.92 1.45 (0.133, 0.091) 11 Experimental Example 214 Comparative BH-3 ET-2 4.82 1.44 (0.133, 0.090) 10 Experimental Example 215 Comparative BH-3 ET-3 4.46 1.64 (0.133, 0.091) 13 Experimental Example 216 Comparative BH-3 ET-4 4.50 1.62 (0.133, 0.091) 13 Experimental Example 217 Comparative BH-3 ET-5 4.42 1.96 (0.133, 0.090) 31 Experimental Example 218 Comparative BH-3 ET-6 4.59 1.59 (0.133, 0.091) 20 Experimental Example 219 Comparative BH-3 ET-7 4.64 1.57 (0.133, 0.091) 19 Experimental Example 220 Comparative BH-3 ET-8 4.42 2.04 (0.133, 0.090) 35 Experimental Example 221 Comparative BH-3 ET-9 4.73 1.55 (0.133, 0.091) 19 Experimental Example 222 Comparative BH-3 ET-10 4.87 1.51 (0.133, 0.091) 37 Experimental Example 223 Comparative BH-3 ET-11 5.16 1.49 (0.133, 0.090) 28 Experimental Example 224 Comparative BH-3 ET-12 5.16 1.18 (0.133, 0.091) 8 Experimental Example 225 Comparative BH-3 ET-13 4.66 2.89 (0.133, 0.091) 32 Experimental Example 226 Comparative BH-3 ET-14 4.61 2.92 (0.133, 0.090) 29 Experimental Example 227 Comparative BH-3 ET-15 4.89 2.83 (0.133, 0.091) 33 Experimental Example 228 Comparative BH-3 ET-16 4.94 2.78 (0.133, 0.091) 33 Experimental Example 229 Comparative BH-3 ET-17 4.99 2.69 (0.133, 0.090) 34 Experimental Example 230 Comparative BH-3 ET-18 4.84 2.72 (0.133, 0.091) 34 Experimental Example 231 Comparative BH-3 ET-19 4.86 1.57 (0.133, 0.091) 25 Experimental Example 232 Comparative BH-4 ET-1 4.45 1.57 (0.133, 0.092) 20 Experimental Example 233 Comparative BH-4 ET-2 4.36 1.56 (0.133, 0.091) 19 Experimental Example 234 Comparative BH-4 ET-3 4.03 1.78 (0.133, 0.092) 23 Experimental Example 235 Comparative BH-4 ET-4 4.07 1.76 (0.133, 0.092) 23 Experimental Example 236 Comparative BH-4 ET-5 3.99 2.13 (0.133, 0.091) 55 Experimental Example 237 Comparative BH-4 ET-6 4.16 1.72 (0.133, 0.092) 35 Experimental Example 238 Comparative BH-4 ET-7 4.20 1.71 (0.133, 0.092) 34 Experimental Example 239 Comparative BH-4 ET-8 4.00 2.22 (0.133, 0.091) 63 Experimental Example 240 Comparative BH-4 ET-9 4.28 1.69 (0.133, 0.092) 34 Experimental Example 241 Comparative BH-4 ET-10 4.40 1.64 (0.133, 0.092) 66 Experimental Example 242 Comparative BH-4 ET-11 4.67 1.62 (0.133, 0.091) 50 Experimental Example 243 Comparative BH-4 ET-12 4.67 1.28 (0.133, 0.092) 14 Experimental Example 244 Comparative BH-4 ET-13 4.21 3.14 (0.133, 0.092) 58 Experimental Example 245 Comparative BH-4 ET-14 4.17 3.17 (0.133, 0.091) 52 Experimental Example 246 Comparative BH-4 ET-15 4.42 3.08 (0.133, 0.092) 59 Experimental Example 247 Comparative BH-4 ET-16 4.47 3.01 (0.133, 0.092) 60 Experimental Example 248 Comparative BH-4 ET-17 4.51 2.92 (0.133, 0.091) 61 Experimental Example 249 Comparative BH-4 ET-18 4.38 2.95 (0.133, 0.092) 61 Experimental Example 250 Comparative BH-4 ET-19 4.39 1.71 (0.133, 0.092) 45 Experimental Example 251

As shown in Table 1, the compound of Chemical Formula 1 of the present disclosure can be used in an organic material layer corresponding to the light emitting layer of an organic light emitting device.

As shown in Table 1, the compound of Chemical Formula 2 or 3 of the present disclosure can be used in an organic material layer capable of simultaneously performing electron injection and electron transport of an organic light emitting device.

When comparing Experimental Examples 1 to 100 and Comparative Experimental Examples 96 to 175 of Table 1, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula 1 of the present disclosure had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which only an aryl group is substituted in the light emitting layer.

When comparing Experimental Examples 1 to 100 and Comparative Experimental Examples, 1 to 11, 20 to 30, 39 to 49, 58 to 68, 77 to 87, 176 to 186, 195 to 205, 214 to 224, and 233 to 243 of Table 1, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula 2 or 3 of the present disclosure had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which a phenyl group less than quaterphenyl is substituted between Ar₂ and Ar₃.

When comparing Experimental Examples 1 to 100 and Comparative Experimental Examples 12 to 17, 31 to 36, 50 to 55, 69 to 74, 88 to 93, 187 to 192, 206 to 211, 225 to 230, and 244 to 249 of Table 1, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula 2 or 3 of the present disclosure had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which quaterphenyl is substituted at a different substitution position from the present disclosure.

When comparing Experimental Examples 1 to 100 and Comparative Experimental Examples 18, 37, 56, 75, 94, 193, 212, 231, 250 of Table 1, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula 2 or 3 of the present disclosure had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which naphthalene is substituted between Ar₂ and Ar₃.

When comparing Experimental Examples 1 to 100 and Comparative Experimental Examples 19, 38, 57, 76, 95, 194, 213, 232, 251 of Table 1, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula 2 or 3 of the present disclosure had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which heteroaryl is additionally substituted to quaterphenylene.

DESCRIPTION OF SYMBOLS

1: Substrate 2: Anode 3: Hole transport layer 4: Light emitting layer 5: Electron transport and injection layer 6: Cathode 7: Hole injection layer 8: Electron blocking layer 9: Hole blocking layer 

1. An organic light emitting device, comprising: an anode; a hole transport layer; a light emitting layer; an electron transport layer, an electron injection layer, or an electron transport and injection layer; and a cathode, wherein the light emitting layer comprises a compound of the following Chemical Formula 1, and the electron transport layer, the electron injection layer, or the electron transport and injection layer comprises at least one compound of the following Chemical Formula 2 and Chemical Formula 3:

wherein in Chemical Formula 1: Z is O or S; L₁ is a direct bond or a substituted or unsubstituted C₆₋₆₀ arylene; Ar₁ is a substituted or unsubstituted C₆₋₆₀ aryl; R₁ to R₃ are each independently hydrogen, deuterium, or a substituted or unsubstituted C₆₋₆₀ aryl, or two adjacent substituents thereof are combined to form a benzene ring; n is an integer of 0 to 8; m is an integer of 0 to 4; and is an integer of 0 to 3;

wherein in Chemical Formula 2 or 3: R₄ to R₇ are each independently hydrogen or deuterium; p1 to p4 are an integer of 1 to 4; L₂ and L₃ are each independently a direct bond or a substituted or unsubstituted C₆₋₆₀ arylene; and Ar₂ and Ar₃ are each independently a substituent of Chemical Formula 4:

wherein in Chemical Formula 4: X₁ to X₅ are each independently N or C(R₈), wherein at least two of X₁ to X₅ are N; and each R₈ is independently hydrogen, deuterium, a substituted or unsubstituted C₁₋₂₀ alkyl, a substituted or unsubstituted C₆₋₆₀ aryl, or a substituted or unsubstituted C₂₋₆₀ heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or two adjacent R₈s combine to form a benzene ring.
 2. The organic light emitting device of claim 1, wherein L₁ is a direct bond, phenylene, biphenylene, or naphthylene, and the phenylene, biphenylene, or naphthylene is each independently unsubstituted or substituted with deuterium.
 3. The organic light emitting device of claim 1, wherein Ar₁ is phenyl, biphenylyl, naphthyl, or phenanthrenyl, and the phenyl, biphenylyl, naphthyl, or phenanthrenyl is each independently unsubstituted or substituted with deuterium.
 4. The organic light emitting device of claim 1, wherein R₁ to R₃ are each independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents thereof combine to form a benzene ring, and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.
 5. The organic light emitting device of claim 1, wherein: each R₁ is independently hydrogen or deuterium; each R₂ or R₃ is independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents thereof combine to form a benzene ring, and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.
 6. The organic light emitting device of claim 1, wherein the compound of Chemical Formula 1 contains at least one deuterium.
 7. The organic light emitting device of claim 1, wherein the compound of Chemical Formula 1 is any one compound selected from the group consisting of the following compounds:


8. The organic light emitting device of claim 1, wherein Chemical Formula 2 is the following Chemical Formula 2-1, and Chemical Formula 3 is the following Chemical Formula 3-1:

wherein in the Chemical Formula 2-1 or 3-1, L₂, L₃, Ar₂ and Ar₃ are as defined in claim
 1. 9. The organic light emitting device of claim 1, wherein L₂ and L₃ are each independently a direct bond, phenylene, or biphenyldiyl.
 10. The organic light emitting device of claim 1, wherein Ar₂ and Ar₃ are each independently any one selected from the group consisting of:

wherein the above group, R₈ is as defined in claim
 1. 11. The organic light emitting device of claim 1, wherein each R⁸ is independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, or two adjacent R₈s combine to form a benzene ring, and the phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl is each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.
 12. The organic light emitting device of claim 1, wherein Ar₂ and Ar₃ are each independently any one compound selected from the group consisting of:


13. The organic light emitting device of claim 1, wherein the compound of Chemical Formula 2 and the compound of Chemical Formula 3 are any one compound selected from the group consisting of the following compounds: 